I love this so much. For me, Tim's character is way more formed by his early years getting left behind by his parents and thinking about Batman etc. in the ways he did before he officially met them than it is by the spate of deaths they dropped on him. Thank goodness he got out and found this support system--crazy as it is--before Jack woke up and said things like "you're all I've got now."
Thinking of recent events in Red Robin and Tim's reaction to Dick's not even actually firing him, it would have been terrible if Bruce encouraged him to go back to Jack here (as opposed to just being neutral and letting him choose) imo. Tim would on some level have seen that as proof he was somebody Bruce felt like he had to look after and was relieved to hand back to Jack. He already has a hard enough time seeing himself as part of a family. The Bats make him feel like part of one for the first time, but he always feels insecure about it.
This is what I love about Bats in general, the way they all long for a family and can never really feel they won't lose their family again. With Bruce it's more a fear they'll die because he can't protect them from all the evil in the world. With Dick it's more he'll mess up and not be good enough to protect them. But it's still a case of the people going away. Tim's more about people losing interest in him no matter if their legally family.